CA2180649C - Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid - Google Patents
Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid Download PDFInfo
- Publication number
- CA2180649C CA2180649C CA002180649A CA2180649A CA2180649C CA 2180649 C CA2180649 C CA 2180649C CA 002180649 A CA002180649 A CA 002180649A CA 2180649 A CA2180649 A CA 2180649A CA 2180649 C CA2180649 C CA 2180649C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- composition
- ppm
- halogenated acetophenone
- microorganism
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 34
- 150000008062 acetophenones Chemical class 0.000 title claims abstract description 21
- 230000002195 synergetic effect Effects 0.000 title description 17
- 230000000845 anti-microbial effect Effects 0.000 title description 3
- 239000000463 material Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 26
- 244000005700 microbiome Species 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- LJYOFQHKEWTQRH-UHFFFAOYSA-N 2-bromo-1-(4-hydroxyphenyl)ethanone Chemical group OC1=CC=C(C(=O)CBr)C=C1 LJYOFQHKEWTQRH-UHFFFAOYSA-N 0.000 claims description 47
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 14
- 241000894006 Bacteria Species 0.000 claims description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 12
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 12
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 9
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
- 239000012530 fluid Substances 0.000 claims description 8
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 241000223260 Trichoderma harzianum Species 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 6
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 6
- 229960002216 methylparaben Drugs 0.000 claims description 6
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 6
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 6
- 229960003415 propylparaben Drugs 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 5
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 5
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 5
- 239000004287 Dehydroacetic acid Substances 0.000 claims description 5
- 239000005639 Lauric acid Substances 0.000 claims description 5
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 5
- 235000011054 acetic acid Nutrition 0.000 claims description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 229960004365 benzoic acid Drugs 0.000 claims description 5
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims description 5
- 235000015165 citric acid Nutrition 0.000 claims description 5
- 235000019258 dehydroacetic acid Nutrition 0.000 claims description 5
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 5
- 229940061632 dehydroacetic acid Drugs 0.000 claims description 5
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 239000001630 malic acid Substances 0.000 claims description 5
- 235000011090 malic acid Nutrition 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 239000004302 potassium sorbate Substances 0.000 claims description 5
- 235000010241 potassium sorbate Nutrition 0.000 claims description 5
- 229940069338 potassium sorbate Drugs 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 5
- 239000004299 sodium benzoate Substances 0.000 claims description 5
- 235000010234 sodium benzoate Nutrition 0.000 claims description 5
- 239000004334 sorbic acid Substances 0.000 claims description 5
- 235000010199 sorbic acid Nutrition 0.000 claims description 5
- 229940075582 sorbic acid Drugs 0.000 claims description 5
- 229960002703 undecylenic acid Drugs 0.000 claims description 5
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 239000003905 agrochemical Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 238000005553 drilling Methods 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 238000005555 metalworking Methods 0.000 claims description 3
- 239000003348 petrochemical agent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 229920001131 Pulp (paper) Polymers 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229960002446 octanoic acid Drugs 0.000 claims 2
- 229960003885 sodium benzoate Drugs 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 25
- 229940093915 gynecological organic acid Drugs 0.000 description 15
- 235000005985 organic acids Nutrition 0.000 description 15
- 239000002609 medium Substances 0.000 description 14
- 241000223259 Trichoderma Species 0.000 description 11
- 230000003641 microbiacidal effect Effects 0.000 description 8
- -1 tanning liquors Substances 0.000 description 8
- 241000589516 Pseudomonas Species 0.000 description 7
- 239000003139 biocide Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 229960004106 citric acid Drugs 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229940013688 formic acid Drugs 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 229960004275 glycolic acid Drugs 0.000 description 3
- 229940033355 lauric acid Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 229940099690 malic acid Drugs 0.000 description 3
- 229940124561 microbicide Drugs 0.000 description 3
- 229940116315 oxalic acid Drugs 0.000 description 3
- 229940095574 propionic acid Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000006481 glucose medium Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- WGHAPLWNJPAJDE-UHFFFAOYSA-N 2-(2-bromoacetyl)oxyethyl 2-bromoacetate Chemical compound BrCC(=O)OCCOC(=O)CBr WGHAPLWNJPAJDE-UHFFFAOYSA-N 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- SIHKVAXULDBIIY-UPHRSURJSA-N [(z)-4-(2-bromoacetyl)oxybut-2-enyl] 2-bromoacetate Chemical compound BrCC(=O)OC\C=C/COC(=O)CBr SIHKVAXULDBIIY-UPHRSURJSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000005473 octanoic acid group Chemical group 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/186,917 | 1994-01-27 | ||
| US08/186,917 US5441981A (en) | 1994-01-27 | 1994-01-27 | Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid |
| PCT/US1995/000989 WO1995020319A1 (en) | 1994-01-27 | 1995-01-24 | Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2180649A1 CA2180649A1 (en) | 1995-08-03 |
| CA2180649C true CA2180649C (en) | 2002-01-15 |
Family
ID=22686823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002180649A Expired - Fee Related CA2180649C (en) | 1994-01-27 | 1995-01-24 | Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US5441981A (de) |
| EP (1) | EP0741517B1 (de) |
| JP (1) | JPH09508621A (de) |
| CN (1) | CN1074899C (de) |
| AT (1) | ATE168528T1 (de) |
| AU (1) | AU683719B2 (de) |
| BR (1) | BR9506607A (de) |
| CA (1) | CA2180649C (de) |
| CZ (1) | CZ286444B6 (de) |
| DE (1) | DE69503603T2 (de) |
| DK (1) | DK0741517T3 (de) |
| ES (1) | ES2119393T3 (de) |
| FI (1) | FI117037B (de) |
| MX (1) | MX9602877A (de) |
| NZ (1) | NZ279439A (de) |
| SK (1) | SK98696A3 (de) |
| WO (1) | WO1995020319A1 (de) |
| ZA (1) | ZA9410122B (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0752853B1 (de) * | 1993-03-10 | 2005-09-21 | Smithkline Beecham Corporation | Phosphodiesterase des menschlichen gehirns |
| US20020068351A1 (en) * | 1994-03-10 | 2002-06-06 | Smithkline Beecham Corporation | Human brain phosphodiesterase |
| US5661149A (en) * | 1995-12-29 | 1997-08-26 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing 1-hydroxymethylpyrazole and a preservative |
| US6235299B1 (en) * | 1998-02-27 | 2001-05-22 | Buckman Laboratories International Inc | Potentiation of biocide activity using diethanolamide |
| US6121197A (en) * | 1999-05-24 | 2000-09-19 | Creanova Inc. | Biocidal composition |
| US6121198A (en) * | 1999-05-24 | 2000-09-19 | Creanova Inc. | Synergistic composition of biocides |
| US6310013B1 (en) | 1999-10-27 | 2001-10-30 | Ecolab Inc. | Lubricant compositions having antimicrobial properties and methods for manufacturing and using lubricant compositions having antimicrobial properties |
| US6610314B2 (en) | 2001-03-12 | 2003-08-26 | Kimberly-Clark Worldwide, Inc. | Antimicrobial formulations |
| FI116560B (fi) * | 2001-06-19 | 2005-12-30 | Kemira Oyj | Puunkäsittelyliuos ja menetelmä puun säilyvyyden parantamiseksi |
| US6967189B2 (en) | 2002-11-27 | 2005-11-22 | Ecolab Inc. | Buffered lubricant for conveyor system |
| EP2001962A2 (de) * | 2006-04-04 | 2008-12-17 | The Sherwin-Williams Company | Geruchsschwache latexfarbe zur unterdrückung von innenraumgerüchen |
| US20090203812A1 (en) * | 2008-02-12 | 2009-08-13 | Lei Rao | Salts of Dehydroacetic Acid as an Antimicrobial for Plastics |
| NZ705670A (en) | 2012-09-25 | 2018-07-27 | Buckman Laboratories Int Inc | Method and system for the enhancement of the biocidal efficacy of monoalkyldithiocarbamate salts |
| EP3696276A1 (de) | 2013-02-25 | 2020-08-19 | Novartis AG | Neuartige androgenrezeptormutation |
| EP2774481B1 (de) * | 2013-03-08 | 2018-06-13 | Symrise AG | Antimikrobielle Zusammensetzungen |
| US11008277B2 (en) * | 2016-06-13 | 2021-05-18 | Syneurx International (Taiwan) Corp. | Co-crystals of sodium benzoate and uses thereof |
| CA3113469A1 (en) * | 2018-08-27 | 2020-03-05 | Symrise Ag | Antimicrobial mixtures comprising at least one hydroxyphenone derivative |
| FR3090272B1 (fr) * | 2018-12-20 | 2022-03-18 | Oreal | Mélange antimicrobien contenant du 4-(3-éthoxy-4-hydroxyphényl)butan-2-one et un composé alcool, et composition le contenant |
| WO2020127383A1 (fr) | 2018-12-20 | 2020-06-25 | L'oreal | Mélange antimicrobien contenant du 4-(3-éthoxy-4-hydroxyphényl)butan-2-one et le 4-hydroxyacétophenone, et composition le contenant |
| CA3131978A1 (en) | 2019-03-12 | 2020-09-17 | Symrise Ag | An antimicrobial mixture |
| EP4682260A1 (de) * | 2024-07-19 | 2026-01-21 | Symrise AG | Antimikrobielles lactobacillus-ferment |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL125192C (de) * | 1963-07-01 | |||
| US3231509A (en) * | 1964-06-11 | 1966-01-25 | Betz Laboratories | Slimicidal composition and method |
| GB1160430A (en) * | 1966-12-23 | 1969-08-06 | Bp Chemicals U K Ltd Formerly | Inhibition of Mould Growth on Crops and Animal Feedstuffs. |
| JPS58183606A (ja) * | 1982-04-21 | 1983-10-26 | Kumiai Chem Ind Co Ltd | 非医療用防菌防藻剤 |
| US4847088A (en) * | 1988-04-28 | 1989-07-11 | Dow Corning Corporation | Synergistic antimicrobial composition |
| DE4026756C2 (de) * | 1990-08-24 | 1995-03-23 | Turner Gmbh | Konservierungsmittel und deren Verwendung |
| CA2054523A1 (en) * | 1990-11-27 | 1992-05-28 | Samuel E. Sherba | Antimicrobial compositions comprising fatty acids and isothiazolones and methods of controlling microbes |
| US5366995A (en) * | 1991-05-01 | 1994-11-22 | Mycogen Corporation | Fatty acid based compositions for the control of established plant infections |
| NZ240355A (en) * | 1991-06-04 | 1994-09-27 | Ecolab Inc | Sanitising composition comprising sorbic and benzoic acids |
-
1994
- 1994-01-27 US US08/186,917 patent/US5441981A/en not_active Expired - Lifetime
- 1994-12-20 ZA ZA9410122A patent/ZA9410122B/xx unknown
-
1995
- 1995-01-24 CA CA002180649A patent/CA2180649C/en not_active Expired - Fee Related
- 1995-01-24 JP JP7520141A patent/JPH09508621A/ja not_active Ceased
- 1995-01-24 AU AU16070/95A patent/AU683719B2/en not_active Ceased
- 1995-01-24 DK DK95908117T patent/DK0741517T3/da active
- 1995-01-24 CZ CZ19962217A patent/CZ286444B6/cs not_active IP Right Cessation
- 1995-01-24 DE DE69503603T patent/DE69503603T2/de not_active Expired - Lifetime
- 1995-01-24 SK SK986-96A patent/SK98696A3/sk unknown
- 1995-01-24 EP EP95908117A patent/EP0741517B1/de not_active Expired - Lifetime
- 1995-01-24 ES ES95908117T patent/ES2119393T3/es not_active Expired - Lifetime
- 1995-01-24 NZ NZ279439A patent/NZ279439A/en not_active IP Right Cessation
- 1995-01-24 AT AT95908117T patent/ATE168528T1/de not_active IP Right Cessation
- 1995-01-24 WO PCT/US1995/000989 patent/WO1995020319A1/en not_active Ceased
- 1995-01-24 MX MX9602877A patent/MX9602877A/es unknown
- 1995-01-24 CN CN95192214A patent/CN1074899C/zh not_active Expired - Fee Related
- 1995-01-24 BR BR9506607A patent/BR9506607A/pt not_active IP Right Cessation
- 1995-06-06 US US08/468,662 patent/US5527826A/en not_active Expired - Lifetime
-
1996
- 1996-06-17 US US08/664,543 patent/US5654330A/en not_active Expired - Lifetime
- 1996-07-26 FI FI962991A patent/FI117037B/fi not_active IP Right Cessation
-
1997
- 1997-03-03 US US08/810,673 patent/US5726206A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NZ279439A (en) | 1998-05-27 |
| FI117037B (fi) | 2006-05-31 |
| ATE168528T1 (de) | 1998-08-15 |
| AU1607095A (en) | 1995-08-15 |
| ZA9410122B (en) | 1995-12-12 |
| FI962991A0 (fi) | 1996-07-26 |
| US5726206A (en) | 1998-03-10 |
| JPH09508621A (ja) | 1997-09-02 |
| DE69503603D1 (de) | 1998-08-27 |
| CA2180649A1 (en) | 1995-08-03 |
| EP0741517B1 (de) | 1998-07-22 |
| FI962991L (fi) | 1996-07-26 |
| CN1144455A (zh) | 1997-03-05 |
| AU683719B2 (en) | 1997-11-20 |
| US5441981A (en) | 1995-08-15 |
| CN1074899C (zh) | 2001-11-21 |
| MX9602877A (es) | 1997-06-28 |
| DE69503603T2 (de) | 1998-11-26 |
| CZ286444B6 (en) | 2000-04-12 |
| BR9506607A (pt) | 1997-09-09 |
| DK0741517T3 (da) | 1998-11-16 |
| ES2119393T3 (es) | 1998-10-01 |
| CZ221796A3 (en) | 1997-02-12 |
| SK98696A3 (en) | 1997-02-05 |
| US5654330A (en) | 1997-08-05 |
| WO1995020319A1 (en) | 1995-08-03 |
| US5527826A (en) | 1996-06-18 |
| EP0741517A1 (de) | 1996-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2180649C (en) | Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid | |
| AU680948B2 (en) | Synergistic antimicrobial compositions containing 2-(thiocyanomethylthio)benzothiazole and an organic acid | |
| US5874453A (en) | Synergistic antimicrobial compositions containing a dimethylamide of a carboxylic acid with mixture of 2-(thiocyanomethylthio) benzothiazone and methylenebis (thiocyanate) | |
| EP0741518B1 (de) | Synergistische antimikrobielle zusammensetzung die methylen-bis-thiocyanat enthält | |
| MXPA96003022A (en) | Antimicrobial compositions synergistic quecontain methylene-bis- (thiocianate) and an acidoorgan | |
| US5929073A (en) | Synergistic antimicrobial compositions containing dodecylmorpholine a salt thereof and dodecylamine or a salt thereof | |
| AU766899B2 (en) | Synergistic antimicrobial compositions containing methylene-bis(thiocyanate) and an organic acid | |
| MXPA00002301A (en) | Synergistic antimicrobial compositions containing dodecylmorpholine or a salt thereof and dodecylamine or a salt thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |